Water → 1H-Pyrrolo[2,3-B]pyridine-3-carboxaldehyde, 5-chloro-1-(phenylsulfonyl)-

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Reaction Steps

To 5-chloro-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (114, 3.60 g, 19.9 mmol) in 100 mL of dichloromethane, potassium hydroxide (50 mL, 9M aqueous, 0.45 mol), tetrabutylammonium hydrogen sulfate (400 mg, 1.0 mmol) and benzenesulfonyl chloride (11, 2.9 mL, 23.0 mmol) were added. The reaction was stirred at room temperature for 3 hours, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was washed with ethyl acetate to provide the desired compound as a white solid (115, 2.3 g).

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